The author of 'Act Three' says you should figure out why you're stymied and look for work-arounds

So you’re in your 50s or 60s and thinking it’s time to take a big step in your career.

Maybe you’ve spent years raising your family, the kids are out of the house and you’re ready to go back to paid work (or to get a paying job for the first time). Perhaps you have an itch to start a business. Or to switch careers.

I caught up with Shifman while she was in New York City, and we discussed the subject.

Next Avenue: You call some of the things that hold people back “pre-existing conditions.” What do you mean by that?

Shifman: These are the kinds of external forces that you have to address or they can derail you. Maybe you say to yourself that you can’t go back to work because you have to let the dog out every day at 3 p.m., or because you might need to take care of your mother during the day.

Ask yourself: "If I could do anything that I wanted to do, what would stop me? What would get in my way?" Then write down everything that comes into your head for the next five minutes. And then think of ways to address each item on your list.

If you think about all the things that could get in the way and then come up with a work-around to resolve each one, you have a much better chance of success. There’s usually a solution.

You write about a woman who is held back because she worries about taking time or money away from her family to do something that might not be successful. What do you say to someone like that?

She should explore why she thinks she’s not worth it. Some people think once they get beyond a certain age it’s not worth investing in themselves. That’s a terrible attitude. We should all be investing in ourselves to learn and grow.

Some of these women deep down don’t think they’re going to make it. I like to ask the question: What are the downsides if you go for it and fail? If they say they’d lose money, I ask: ‘Can you live with that?’ If they say ‘I’d be really embarrassed that people would know I tried and failed,” I say: ‘Would your kids still love you?’ Once they go through the list of their potential downsides they often say, ‘Oh, that’s not so bad.’

You surveyed more than 1,000 college-educated women over 45 considering Third Acts and 19 percent said their spouse was holding them back. How can women overcome this problem?

Often, men’s careers head up and up and up and then in their mid-50s, things start to even off and come down. At that same time, their wives get a re-energized look at life and want to start things up again. And that creates a disconnect in the marriage.

Some husbands are unhappy about changing their way of life to pick up the slack as their wives become busier. In the book, I mention a woman whose husband is an anesthesiologist and wasn’t interested in renegotiating their sharing of chores so she could work. He said to his wife: “Why should I have to pick up the dry cleaning so you can make $30,000 a year, which we really don’t need?”

If you have a husband like that, you may need to hire someone to pick up the slack. Alternatively, maybe getting a job isn’t right for your family’s situation. Or maybe it's time to put your project on the back burner while you do some marriage counseling.

More than 40 percent of the women you surveyed said a fear of rusty skills held them back. I’m sure many men feel this way too. How can people keep current with technology in midlife?

Of all the things that could hold you back, technology is the easiest one to solve. You can take a class at a community college or a self-directed course online. When I wanted to learn how to use Excel, I took a self-directed class online from Microsoft.

That’s different from social-media skills. I haven’t found that social media skills really hold people back. Just about any office environment has young whiz kids who are doing that stuff. They wouldn’t expect someone in their 50s or 60s to become their Twitter person.

You say that sometimes it just isn’t the right time to make a big career move. How can people tell if that’s the case and when should they reconsider the idea?

It’s possible that this just isn’t a good time for you to start a new career or a business. Maybe you are your mother’s primary caregiver or have other reponsibilities.

If you can’t come up with a work-around to what’s holding you back, that means this isn't the time. It doesn’t mean it won’t ever be the time. In six months, sit down and take a fresh look at your life. If things have changed, you just might be able to give your next act a try.

Richard Eisenberg is the Senior Web Editor of the Money & Security and Work & Purpose channels of Next Avenue and Managing Editor for the site. He is the author of How to Avoid a Mid-Life Financial Crisis and has been a personal finance editor at Money, Yahoo, Good Housekeeping, and CBS MoneyWatch.@richeis315